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Why the Best Leaders Show Their Weaknesses

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The Leadership Insiders network is an online community where the most thoughtful and influential people in business contribute answers to timely questions about careers and leadership. Today’s answer to the question, “How do you exude confidence at work when you’re feeling insecure?” is written by Dennis Yang, CEO of Udemy.

In the foreword to the reprint of Intel cofounder Andy Grove’s High Output Management, investor Ben Horowitz recalls Grove telling him, “CEOs always act on leading indicators of good news, but only act on lagging indicators of bad news. … In order to build anything great, you have to be an optimist.”

I agree that CEOs need to be optimists, but we need to be realists too, especially for the people helping us build that next great thing. When leaders face doubts, they should acknowledge the challenges ahead while still making it clear that they have strategies for overcoming them. That’s real confidence, not fakery.

 

Learn your way to confidence

Most startup CEOs consider themselves entrepreneurial, and entrepreneurs have to become great salespeople in order to gain the buy-in of investors, employees, and customers. Convincing strangers to spend their hard-earned money on a company they’ve never heard of requires some serious confidence, and it often doesn’t come naturally. Most CEOs have an advanced degree like an MBA, but formal education still can’t equip someone with authentic confidence.

Learning is what I prescribe for any major lack of confidence. Doing broadcast media interviews, for example, had been a source of insecurity for me, but I knew I’d be representing Udemy more and more as we grew. Understanding the secrets of great public speakers has made a tremendous difference in how I come across when communicating. So I took a bunch of public speaking courses and practiced doing mock media interviews with our internal communications director, as well as a few former journalists; eventually my nerves disappeared. If something makes you feel insecure, immerse yourself in it until you gain the upper hand.

 

Find people to confide in

When you’re a startup CEO, you get used to guiding the company through many firsts. Sometimes you can draw upon past experience, and sometimes you realize just how much you still have to learn. In the latter case, it’s invaluable to have a trusted panel of mentors and advisors. My professional network offers me a safe space for working through questions and testing ideas, so that by the time I’m in front of my direct reports and the rest of the company, I can project confidence and clarity about what we’re going to do next.

 

Be transparent

I value authenticity a lot, and I’m not good at pretending everything is rosy when it’s not. At the same time, part of my job as CEO is to instill confidence that I can steer our ship through any storm. What works for me is to directly admit the challenges ahead, but always present them in tandem with real, thought-out plans and solutions. We’re always going to encounter rough patches, but no one on my team is afraid of hard work. Having a clear plan of attack for moving past roadblocks motivates them. Maintaining a false facade is exhausting and self-defeating.

 

Vulnerability is okay

Shouldn’t a CEO be an all-powerful, infallible superhero who never suffers through a crisis or loses confidence? I don’t think so. A fundraising pitch probably isn’t the right time to show your vulnerability, but there are plenty of other times when being dead certain can actually backfire.

The most obvious area is innovation. Innovative ideas never emerge fully formed and ready for implementation, and they rarely come from the top. In our business, we believe that the wisdom of the crowd is greater than a single individual’s. The messy work of experimenting, measuring, and trying again is the lifeblood of startups. If I set an example of never questioning our decisions, no one else would feel comfortable doing so and we’d stagnate as an organization.

If leaders project nothing but confidence — even when everyone knows things aren’t going well — those leaders will lose credibility and mute voices of dissent. So I don’t sweat it too much when I’m feeling less than completely self-assured. It is a good reminder that we’re all part of a group effort, makes me more approachable, and opens the door for others to contribute.